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Kelsey MacDermaid, Content Creator

FLARE #HowIMadeIt celebrates 100+ talented, ambitious and driven Canadian women with cool jobs. Want what Kelsey has? Here’s how she did it

Kelsey MacDermaid; Toronto;

Let’s say we’ve just met at a cocktail party. How would you describe, in a nutshell, what you do?

I run a digital media company with my best friend Becky Wright. We create DIY videos on how to make anything and everything trendy, seasonal and desirable. We upload our tutorials on YouTube, under the name The Sorry Girls, so we’re often called YouTubers.

Where did you go to school and what did you study?

I went to Humber College where I received a B.A. in film and media production.

What was your first paying gig out of school? (In your field, or not.)

I was super lucky to get out a job at the same place I did my internship. I worked as a production coordinator at a commercial production company (i.e. making television ads).

What was your BIG break? How did you land it?

In 2014 we were invited on The Marilyn Denis Show. At the time our peers, colleagues, and even parents started to realize what we were doing was really amazing and unique. It wasn’t an obvious game changer at the time but it did introduce us to a broad new audience and allowed us to try our craft in a live TV setting. Most importantly, I think it transformed how we looked at ourselves and how others saw us.

Describe the moment in which you first realized, I think this is actually going to work out?

Good question. HGTV star extraordinaire Scott McGillivray actually reached out to us because he kept hearing our name tossed around for a possible HGTV show (p.s. this hasn’t happened… yet). He took us out to lunch and had lots of amazing advice to give but also told us that we were in the right space as we were in control of our own content and didn’t have to answer to anyone but ourselves. He told us to keep doing what we’re doing and that we’ll go really far. That meant a lot to me and was one of the pushes I need to decide I was ready to quit my job and go full-time with The Sorry Girls.

What would you say has been your biggest failure or shortcoming, career-wise, to date? How did you bounce back?

I think our biggest shortcoming historically was not testing our limits hard enough or fast enough. I’ve learned that you really do have to take risks and spend money to make money. In our case we are finally putting that money into equipment, our team and new ventures.

Name one piece of career advice you always give.

Work your little butt off, care about what you do and—even though you might hate it—network.

What’s the worst career advice you’ve ever gotten?

I don’t think I’ve been directly told this but growing up we are rewarded for doing amazing things on our own, as if it’s better if you did it alone versus with a team. That might be working hard but it’s definitely not smart. Surrounding yourself with smart and dedicated people is the best thing you can do for your career.

Did you deal with barriers in your field because you are a woman? If so, what were they?

Where do we start? We have to make frequent trips to the hardware store, and the treatment we get there is actually hilarious. Not necessarily by the employees but often by men buying supplies for their own projects. “Who is going to build that for you?” is something we got asked on a recent trip. Banks are also the worst. I don’t know if it’s because we are women, or young, or in a new field, but it’s like our money is no good to them. It’s ridiculous. We’re blowing up and our bank won’t keep up or even try.

Are you making a fair income for your work? Why or why not? Do you have a side hustle for extra cash? If so, what is it?

It was tough when we first went full-time at the end of the summer in 2015, and it was a big day when I started making more than I was when I worked as a production coordinator. Our company as a whole is now making a good amount of money and we’re growing, in terms of our team and ambitions. It’s so crazy to see this thing we started from nothing bringing in cash that will not only pay my bills but also the bills of everyone else we work with!

What’s the worst stereotype you’ve heard about millennials at work?

That we’re lazy. Our team works hard but we also try to have a healthy work-life balance.

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